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Winter To Spring Transitional Outfits We Want To Wear Right Now

Not to pull back the curtain too much, but a lot of our posts are born from the things we would want to read. So the other day at a team lunch, we were sitting outside while it was 55 degrees (freezing by our standards) and we were talking about winter to spring transitional outfits. I often forget that layers are a thing, and I will go from full winter clothes to wanting to wear denim shorts and a tank top just to protest cold weather. But transitional outfits are indeed a thing and the key is layers. So we thought it’d be fun to pull together some winter-to-spring looks to inspire ourselves and you.

So who wants to play imaginary dress up?? I’ll start.


1. Marieta Top | 2. The Siena Tank | 3. Stan Ray Painter Pant | 4. Stan Ray 4-Pocket Shop Jacket | 5. Square Toe Leather Boots | 6. Line Dangle Earring | 7. Initial Necklace | 8. Organic Ono Ono – Multi-Benne Stain

I fully love men’s utility pants and especially love wearing them with feminine pieces. For my first imaginary look, I chose these painter pants and matching shop jacket, and a fitted tank top layered under this mock neck that I have been coveting for quite some time. For accessories, I am very into these western-style boots, a gold initial necklace (from this new brand that I LOVE), drape-y earrings, and a bold lip. It’s taking a lot of restraint to not click purchase on every one of these items.

1. Marquise Linen Dress in Micro Polka Dot | 2. Brenna Over-The-Knee Boots | 3. Badass Iconic Lipstick | 4. The Long Mac Coat | 5. Medallion Pearl Necklace | 6. CZ Lock Huggies | 7. Wave Ring

My more dressed-up look is inspired by the tall boot trend and this photo that I saw on the internet. I’ve been wanting to experiment with trench coats too, so why not throw that in the mix. All the jewelry is from this Black-owned jewelry brand, Ten Wilde, that I can’t get enough of. They make really elegant, unique, and actually affordable jewelry and I want basically everything. The dress is by the brand Sleeper that makes the most beautiful pajamas I have ever seen but they also make sweet prairie dresses like this one. The boots are something from my dreams (and a splurge) but boy are they beautiful.


I always say (or at least think) that I want more fun colors in my wardrobe but have only kinda been successful at it. So despite my desires, I realized that I’m simply not a natural at actually putting together outfit looks that are in line with how I want to dress. Hence why putting these two outfits together took me a comical amount of time. But honestly, I’m really happy with them and really want them on my body ASAP. Practice makes perfect? Or a little better at least?

1. Denim Faux Shearling Trim Jacket | 2. Iga Personalized Pinky Ring | 3. Basit Ring | 4. High Rise Dad Jeans | 5. Daelyn Lug Sole Short Boot | 6. Satin Lace Top | 7. Battenberg Cardi | 8. The Sydney Zip-Top Crossbody Bag | 9. The Gidi Chain | 10. Initial Lock Necklace | 11. Romee Necklace

So with this “casual look”, the fun is in the details. Those shearling cuffs and collar on that denim jacket are so cute (and the darker denim makes it a great nighttime jacket too). Then I’ve been eyeing those jeans for a minute and might just do it. They look so cool, are high-waisted and rigid denim which I’ve really been wanting. Pretty over the stretch. Anyone else? The next thing I fell for was that sweater (#forevercheckered). It’s hip but not too in your face with it and since it’s a cardigan, I thought that pretty pink satin cami could be a great pop of color if I wanted it unbuttoned or have it be a great “night” option where you could just ditch the sweater if I wanted to feel a little sexier. Can you say layers?? I also love that cute yellow crossbody (I wish I liked clutches but I hate having to carry them) and those boots are riiight up my alley. They aren’t necessarily a “night shoe” but with a quick change, this is easily a day-to-night outfit. Oh and let’s not forget the jewelry! I love necklace layering and all of these pieces are SO GOOD. I am also a ring lover but somehow I misplaced my collection (or they got stolen) on my last big trip in 2019. Needless to say, I need to replace them because I miss wearing them.

1. Sherpa Jacket | 2. Iga Personalized Pinky Ring | 3. Basit Ring | 4. Melody Leather Crossbody | 5. Shoko Sweater | 6. Essential Chelsea Boots | 7. Strappy heeled sandals. | 8. The Gidi Chain | 9. Harris Reed Star Crossed Pearl Necklace | 10. Romee Necklace

Let’s dress up but still keep it casual. I’m not fully at the point where I’m really dressing it up for super fancy parties or outings. But I do love to dress up a little and wearing a dress is my way of doing that. I have loved this dress for soooo long. I ordered the sleeveless version last summer but it was the wrong size and I decided that I didn’t really need either at the time. So I didn’t exchange it despite my heart wanting me to. But I will say the quality is incredible and it has a great weight to it. Welp, I might have talked myself back into it. Oh, and can you tell I love denim shearling jackets? I like how this one is a little longer and a lighter wash for springtime. Now, if I wanted to wear this outfit for a more casual day or night event I would choose those blue boots. See, color! But for something a little fancier, I really love those green heeled sandals (which happen to work perfectly with that cute little green bag that looks like it can actually hold the essentials). I did switch out one of the necklaces to dress this look up. I love all of the jewelry from that brand.


1. Sweater | 2. Gold Ring | 3. Gold Ring Set | 4. Asymmetrical Jeans | 5. White Booties | 6. Dope Leather Jacket | 7. Bucket Bag | 8. Gorjana Necklace

Ah, welcome to the look of my dreams. I’d feel like a billion dollars walking into a lunch date dressed like this!! Also, who do I think I am to put a $600 leather jacket in here? I’m just a girl who’s been wearing a $90 leather jacket for 7+ years and it’s officially shedding its leather so I’m in the market for a new one and a girl can dream OKAY!? And this one is truly perfect. I’ve been eyeing checkered sweaters like this ever since I saw Julie and Sara wearing one that they bought from a local LA boutique that was unfortunately out of stock (I looked!!). This one is very affordable and I’m obsessed with it…hoping they get more sizes in soon (or if you know of any similar ones please comment because I’m ready to add one like this to cart). I’ve been eyeing these Urban Outfitters boots ever since we did the tall boot post (these are the short version of one of the tall boots in the roundup). Lastly, the asymmetrical jean trend is one I am ready to hop aboard on. What do you think?? And I heard Abercrombie has made a comeback (especially in the denim department!). Oh and PS I have this necklace and wear it ALL the time!

1. Balconette Bodysuit | 2. Ring | 3. Gold Ring Set | 4. Pants | 5. Shoes | 6. Earrings | 7. Blazer | 8. Clutch

This one is certainly the ‘risker’ look out of my two outfits. I’ve been SUPER into this font-slit pant style but have yet to buy a pair of my own because it feels like a big commitment for a trend that will go out of style eventually (especially since it’s more of an ‘occasion’ look versus the more everyday but still very ‘trendy’ asymmetrical jeans in the last look). The lace bodysuit is SO cute (I’ve been eyeing it for a while and even tried it on at the Fleur Du Mal store!) It’s very comfortable and good quality, plus it’s beyond flattering for all kinds of body types (both of the employees there were wearing it when I came in). I’m in love! Overall though, what do ya think of this look? Would you wear this risky but cool outfit or something similar??


1. White Top | 2. 9″ Rise Skinny Jeans | 3. Swing Coat | 4. Heart-Shaped Purse | 5. Boyfriend Bold Chain Necklace | 6. Gumball Pearl Ring | 7. Floral Flats | 8. Lip Color

Those shoes were my jumping-off point – they’re SO. FREAKING. CUTE. Kate Spade keeps targeting me with ads and let me tell you – they’re working. I’m a sucker for a super dark wash jean, an oversized white top, and those two pieces of jewelry are already my go-to daily pieces. I even own the purse already (thanks, mom, for nailing it this Christmas)! I’m obsessed with Jennifer Diederich’s quick escape coats – I splurged on one last year and know that it’ll keep making me smile for years to come. This one is expensive, but it’s so timeless and cheery – I’ll be saving up to add it to my closet this year!

1. Collared Mini Dress | 2. Rattan Woven Bag | 3. Clogs | 4. Lip Color | 5. Pearl and Diamond Necklace | 6. 3 Ring Set | 7. Oversized Rattan Barrette

First off, let me sing the praises of the long-sleeved dress as a transitional piece. I don’t know how they keep me SO much warmer than their short- and 3/4-sleeve counterparts, but there’s some magic going on there. Plus, if you’re extra chilly, just throw a bodysuit or leotard of choice on underneath. MAGIC. Beyond that, these clogs are my current go-to pair of shoes – they’re loud (appearance-wise) but super comfortable, and they look awesome paired with a similar red/pink dress I own. I’m going through a huge rattan accessory phase right now, too – this bag and barrette are so fun. And in case you’re not familiar, The Lip Bar’s products RULE – this liquid lipstick is only $14 and it blows my Mac Russian Red + NARS Cruella outta the water. (They’re also a Black-owned business! Check them out!)

Well, I hope was as fun for you as it was for us! Here’s to hoping we all are more prepared for the winter to spring transition. xx

Opener Image Credit: Photo by Veronica Crawford | From: New Fashion On My Body: The One Where I Dressed Like A Fisherwoman, Wore 6 Great Coats, AND An All Star Pair Of Boots

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4 months ago

I am old enough to remember the 1990s styles and it’s horrifying to see them back with a bang. I shall stick with the French / Parisian principles of dressing – style that never goes out of fashion, basic pieces which are expensive, well-made and last a lifetime and being objective about whether things really look good, or if it’s just the collective media telling us that chunky boots look wonderful but in 5 years time will be sooooo passe.

4 months ago
Reply to  Anna

I agree. I suppose also in my colder climate layers mean something different- I am also more capsule oriented and focused on practical clothing.

4 months ago
Reply to  Anna

I’m with you for most of these re-runs, but I did actually keep my lace bodysuit from back in the day and started wearing it again last year. It was just one of those things that was too pretty to get rid of so it’s fun to wear it!

4 months ago

Loved the looks! So fun to think about actually going out for a lunch/dinner date without a mask on! People can actually see your lipcolor! Jess, I think that split color sweater dress would be absolutely stunning on you.

4 months ago

These all feel so fun and fresh and bright!! My style is more classic (erm, boring) but so fun to see what’s trendy right now! I love how you all mixed in “aspirational” pieces with those you actually own or have tried on IRL. And I suppose I could add just one of these pieces to my wardrobe to be slightly less boring 🙂

4 months ago
Reply to  Juanita

And +1 to highlighting Black-owned businesses that you love, more of these please!

4 months ago

Caitlin these SHOES!!!

4 months ago

I’m here for the 90’s (or 80’s) comeback with a twist! I might not wear it but brings back fun memories of going clubbing on South Beach! I wish I kept all those outfits!

4 months ago

Mallory’s dressier look is very exciting! I appreciate seeing how you’d put together sexy, trendy pieces (I already know how to dress “timelessly”)

4 months ago

Mallory, did you mean to write risqué instead of risky? Lol! But I guess either word works!

4 months ago

Those asymmetrical jeans are on their way! What a fun look.

4 months ago

This is a very inspiring post. Thanks for sharing.

4 months ago

I love some inspiration to shop my own closet for something that sparks joy! Sometimes I fall back on comfortable neutrals….sometimes I want a fun pop of color!

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